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Hey Gents,

First off, it’s true, Huckberry has one of the best damn emails out there. I’ve subscribed to a bunch of stuff over the years, but Huckberry’s is one that I look forward to every week.

Make sure to check them out if you haven’t already. (You should see a sweet landing page made especially for EG readers.)

This week’s guest article comes from my friend Kyle of The Distilled Man, a great site to peruse if you’re looking to acquire new manly skills, or hoping to perfect the skills you’re sorta familiar with, but far from mastering.

Take it away, Kyle!

If you’re like most guys, shopping for clothes can sometimes be like speed dating.

You choose your outfits based on a gut feel in a split second. “Yep, that looks like me” or “I could pull that off.” And then you get the hell out of there.

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Photo Credit: Practicalowl via Compfight cc

I used to feel pretty in touch with my personal style because I had this ninja-like ability to find the four shirts in the store that I thought could work for me.

Sure, other things would occasionally catch my eye—pieces that looked cooler or more fashionable. But in my mind I thought, “I don’t know, it might be a bit flashy” or, “It’s just not me.”

The problem was, I’d get home from the store and find that my closet was full of clone shirts. My wardrobe looked like a fabric-swatch booklet for the blue spectrum.

I started to realize that it’s pretty easy to get into a rut when you’re just shopping in your comfort zone.

You think of yourself a certain way, you think your friends perceive you a certain way, and you dress the part. It ends up becoming a self-fulfilling prophesy.- Theodore Roosevelt

So how do you break out of that rut?

Simple answer: You’ve got to step outside of your style comfort zone. …which means forgetting what you thought was “your look” and trying something different.

Here are a few ways to start:

 1. Put Yourself in Expert Hands

Congrats, you’re already doing one of the best things you can do to break out of a rut: follow the advice of experts.

Now the key is taking action.

Without thinking twice, try buying the next 4 outfit combinations featured on EG. Will they all be a perfect fit for you? Maybe not, but you’ll have a chance to try on an entirely different viewpoint. And in that process, you may discover that your look is different than you think.

2. Steal From The Stars

While some people are great at this, others forget that celebrities are like virtual mannequins—demoing looks and styles we can use as a menu of ideas.

It’s not about embracing fleeting trends or the latest fashion. When you borrow a look from a celebrity you respect, you’re also tapping into the ethos or attitude that draws you to them.

Or from a practical standpoint, you can steal ideas from celebrities who are close to your body type. While I’m not a country music fan, I found myself enamored with a particular look by country star Blake Shelton.

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Mister Shelton

Like me, he’s also 6’6”, and he has this signature look where he wears dark jeans with a button-up shirt, suit vest and tie. Sort of dressed-up casual. I thought “Now, there’s another tall man who looks great—I’m going to steal that idea.” 

3. Dress for a Role

One of the best quotes I heard that changed the way I think about style is: “Dress like you belong somewhere.” The idea that your outfit should have a point of view, it’s not just some apology or compromise. You walk into the room and people say, “I get it.”

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Professor Indy

Not too long ago I realized I really dug the “professor” look. It worked for me, and it freed me up when I shopped for clothes.

I wasn’t buying for myself anymore, I was buying for a role.

I would have never bought the same things for myself otherwise. “A v-neck cashmere sweater and sportcoat? Oh that’s not Kyle, he only wears light blue, striped button-up shirts…untucked…with saggy jeans.” 

Buying for a role gives you a cohesive look to shop for, and it gives you permission to ignore your gut feel about what you think your look is.

4. Name Your (Aspirational) Style

Beyond shopping for a role, you can take it a step further by coming up with a specific theme. I’m ashamed to say that my wife and I watch a reality show called Restaurant Impossible—one of those makeover shows where they have 2 days to change the menu and make over the dining room of a failing restaurant. (Note from Barron: No shame necessary. My wife and I watch this show all the time; it’s awesome)

Before the dining room renovations happen, the host, Robert Irvine, always asks his designer for a 2-word theme to describe her vision of the new space. Like “Mediterranean-Americana” or “Hofbrau-Chic.” What’s funny is that they’re usually mash-ups of two totally different ideas.

But somehow, articulating a succinct theme gives them a precise vision of what to go for with the space. And it drives their choices for how to decorate.

You can do the same thing for your wardrobe.

If picking a role like “professor” is too limiting, you can expand it and tweak it with a theme. Your new look could be “Mogul-Philanthropist” or “Nautical-Barista,” or…well, you get the idea.

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Not only does it give you some interesting parameters to work with, but it gets you out of your comfort zone and into an entirely different vision for how to see yourself. 

OK, Is This Really Doable?

I know what you’re thinking: Yeah, this all sounds pretty good, but what will my friends say when I come strutting in wearing these new getups?

Well, I have three pieces of good news for you:

  1. Assuming you don’t have a private jet or a manservant, these changes to your wardrobe are going to happen pretty gradually, a few outfits at a time. And that’s fine, especially if you follow the lean wardrobe principles.
  2. Unless you start dressing like Mad Max, even style changes that seem like a big shift to you probably aren’t that shocking for those around you. Most of your friends will probably just think, “Huh, he finally showered and put on a clean shirt. It works for him…”
  3. Even if your new look feels forced or foreign at first, you’ll make it your own. In his book, Steal Like An Artist, Austin Kleon reminds us that even when we “steal” or “remix” others’ ideas, we ultimately put our own stamp on them, since we’re shaped by the unique mixture of all the influences we love.

I can still remember the day I mustered up the courage to wear bright red slacks to my old office.

To me, they were pretty loud. I thought for sure I would walk in and instantly hear rumblings. “What the hell is he wearing?” As soon as I got to my status meeting, I just KNEW somebody would take the opportunity to give me shit about my colorful trousers.

But to my shock, not a single person commented.

It just wasn’t that big of a deal. Apparently I could pull off colorful pants. Who knew? All this time, it wasn’t the peer pressure from my office mates holding back from a colorful wardrobe. It was me.

To Sum It Up…

Even if you’ve got “your look” down pat, ask yourself: Am I limiting my style by dressing in my comfort zone? Am I in a style rut and don’t even know it?

It’s worth shaking things up a bit. Who knows, you might end up exactly where you started. But if nothing else, you’ll be stronger for stretching the boundaries of your personal style. And you might get a really good story out of it.

What other tricks have you used to break out of your style comfort zone? Were they successful? Share your thoughts in the comments below.

PUBLISHED July 10, 2014


Kyle Ingham is the founder of The Distilled Man, a website dedicated to helping men learn essential “gentlemanly” skills like grilling, cocktails, and etiquette. Click here to get a free copy of his new eBook, “48-Hour Gentleman: Your One-Weekend Plan to More Confidence, Poise, and Manly Know-How.”



  • beardedman

    I think the idea of dressing to a role and putting a name to your aspirational style is brilliant. For me, I want to look something between lawyer-ish and dandy-ish. Put together but comfortable and not too stiff. My role is not completely defined yet, but I’ll get there.

    • http://www.thedistilledman.com/ Kyle Ingham

      @beardedman:disqus Excellent! That’s the fun part about it: defining your style isn’t about a destination—it’s about the journey. In all things, I’m a big fan of the idea of “triangulation”: you try one thing, maybe it’s not quite right, you try another and maybe it’s not perfect either…but in the process you end up finding what DOES work—or at least finding out more about yourself. Cheers! K

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